Five D:C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii MAXIM. and their anti-inflammatory effects
Five triterpenes with a D:C-friedo-oleanane skeleton, D:C-friedo-oleana- 7,9(11)-diene-3β,29-diol (3-epikarounidiol), 7-oxo-D:C-friedo-olean-8-en- 3β-ol (7-oxoisomultiflorenol), 7-oxo-8β-D:C-friedo-olean-9(11)-ene-3α,29- diol, D:C-friedo-olean-8-ene-3α,29-diol (3-epibryonolol), and D:C-friedo- olean-8-ene-3β,29-diol (bryonolol), the first four of which are new naturally occurring compounds, were isolated from the seeds of Trichosanthes kirilowii MAXIM. The structures were determined by spectral and chemical methods. 3-Epikarounidiol, 7-oxoisomultiflorenol, and 3-epibryonolol showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation in mice. The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 μg) was 0.2-0.6 mg/ear.
7-oxodihydrokarounidiol-3-benzoate and other triterpenes from the seeds of cucurbitaceae
The highly-polar fractions of the nonsaponifiable lipids obtained from the methanol extracts of 10 Cucurbitaceae seed materials were investigated for their components. Fourteen dihydroxy triterpenes and their derivatives, and one oxo-sterol were characterized. They are 7-oxodihydrokarounidiol-3-benzoate (7-oxomultiflor-8-ene-3α,29-diol-3-benzoate), isokarounidiol-3-p-methoxybenzoate (multiflora-6,8-diene-3α,29-diol-3-p-methoxybenzoate), karounidiol-3-benzoate, karounidiol, isokarounidiol, 5-dehydrokarounidioI, 7-oxodihydrokaroudnidiol, bryonolol, 3-epibryonolol, loranthol, betulin, 29-hydroxylupeol, erythrodiol, (23Z)-cycloart-23-ene-3β,25-diol and 7-oxositosterol among which the first two were the new naturally occurring compounds. Karounidiol and 7-oxodihydrokarounidiol were detected in all of the investigated seed materials.